Light Induced Diastereoselective Ketoesterification To Access 6,5-Fused Tetrahydrobenzofuranones in Batch and Continuous Flow Conditions

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12628 - 12638

Опубликована: Авг. 15, 2024

Ketoesterification stands as a pivotal technique in organic synthesis, particularly due to its essential role the construction of numerous natural products and bioactive compounds. In this study, we have successfully accomplished visible-light-induced cyclization diastereoselective direct ketoesterification cyclohexadienones, facilitating access cis 6,5-fused tetrahydrobenzofuranone derivatives. The utilization TEMPO radical quenching experiments has provided insights, suggesting an ionic mechanism underlying methodology. Additionally, regioselective addition 2-oxo-2-phenylacetate least hindered side cis-selective fashion makes protocol more appealing toward product development. Incorporation continuous flow reaction into batch notably bolstered efficiency rate. Furthermore, demonstration gram-scale reactions setup synthetic utility with NaOH underscore scalability practical applicability approach.

Язык: Английский

Mn-Catalyzed Electrooxidative Radical Cascade Cyclization for the Synthesis of 6-Phosphorylated Quinoxalino[2,1-b]quinazolin-12-ones

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 12, 2024

Due to their important potential medicinal value, chemists are pursuing mild and efficient methods synthesize structurally diverse quinazolinone derivatives. In this paper, a series of isocyano-tethered

Язык: Английский

Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(15), С. 3303 - 3309

Опубликована: Июнь 15, 2024

Abstract We herein reported, a visible‐light‐induced K 2 S O 8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α ‐oxocarboxylic acids leading to diastereoselective synthesis polycyclic spiroindolines bearing an N ‐formyl unit derivative utilising the alkali metal salt as mediator under mild conditions. This study offers illustration and 3‐(2‐isocyanoethyl)indoles‐based reactions it shows involvement glyoxolate ions without decarboxylation access analogue. The batch process can be extended continuous flow system using glass tube loaded placed between PFA capillary reactor, which greatly advance efficiency even promoted gram‐scale synthesis.

Язык: Английский